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Synthesis 1990; 1990(9): 808-815
DOI: 10.1055/s-1990-27022
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Rearrangement of 3,3-Disubstituted 1-Aryl-4,5-dihydro-5-oxo-3H-1,2,4-triazolium Tetrafluoroborates; Part 2. A Convenient Synthesis of 1,5-Annulated 1,2-Dihydro-2-phenyl-3H-1,2,4-triazol-3-ones

Hubert Gstach* , Patrick Seil
  • *Institut für Organische und Pharmazeutische Chemie, Universität Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria
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Publication Date:
17 September 2002 (online)

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1-Isocyanato-1-(phenylazo)cycloalkanes 3 react with tetrafluoroboric acid to yield 3-spiro substituted 4,5-dihydro-5-oxo-1-phenyl-3H-1,2,4-triazolium tetrafluoroborates 4. Compounds 4 rearrange with ring expansion in good yield to give, after basic workup, 1,5-annulated 1,2-dihydro-2-phenyl-3H-1,2, 4-triazol-3-ones 5.